Citation: Li Li, Chen Qi, Xiong Xiaonan, Zhang Chuang, Qian Jingjing, Shi Jie, An Qiong, Zhang Ming. Synthesis of polysubstituted pyrroles via a gold(Ⅰ)-catalyzed tandem three-component reaction at room temperature[J]. Chinese Chemical Letters, ;2018, 29(12): 1893-1896. doi: 10.1016/j.cclet.2018.09.004 shu

Synthesis of polysubstituted pyrroles via a gold(Ⅰ)-catalyzed tandem three-component reaction at room temperature

Kangda College of Nanjing Medical University, Lianyungang 222000, China

qan@njmu.edu.cn

mingzhang@njmu.edu.cn

Received Date: 16 July 2018
Revised Date: 16 August 2018
Accepted Date: 6 September 2018
Available Online: 8 December 2018

Figures(5)

A gold(Ⅰ)-catalyzed three-component reaction of β-nitrostyrenes with 1,3-dicarbonyl compounds and primary amines to form polysubstituted pyrroles has been developed at room temperature in ethanol. The key advantages of the three-component reaction are the mild reaction conditions and environmentally safer solvent.
- Gold(Ⅰ) complex,
- Multicomponent reaction,
- Nitrogen heterocycles,
- Room temperature,
- Pyrroles
1. [1]
  (a) V. Bhardwaj, D. Gumber, V. Abbot, S. Dhiman, P. Sharma, RSC Adv. 5 (2015) 15233-15266;
  (b) S.S. Gholap, Eur. J. Med. Chem. 110 (2016) 13-31;
  (c) C. Wu, W. Wang, L. Fang, W. Su, Chin. Chem. Lett. 29 (2018) 1105-1112.
2. [2]
  (a) D.J. Ramón, M. Yus, Angew. Chem. Int. Ed. 44 (2005) 1602-1634;
  (b) A. Dömling, Chem. Rev. 106 (2006) 17-89;
  (c) A. Dondoni, A. Massi, Acc. Chem. Res. 39 (2006) 451-463;
  (d) J. Yu, F. Shi, L.Z. Gong, Acc. Chem. Res. 44 (2011) 1156-1171;
  (e) N.N. Zhou, H.T. Zhu, D.S. Yang, Z.H. Guan, Org. Biomol. Chem. 14 (2016) 7136-7149;
  (f) Y.N. Gao, M. Shi, Chin. Chem. Lett. 28 (2017) 493-502;
  (g) Xie J, Jin H, A.S.K. Hashmi, Chem. Soc. Rev. 46 (2017) 5193-5203;
  (h) W.B. Lin, M. Li, L. Fang, C.F. Chen, Chin. Chem. Lett. 29 (2018) 40-46;
  (i) P. Xu, W. Li, J. Xie, C. Zhu, Acc. Chem. Res. 51 (2018) 484-495.
3. [3]
  A. Hantzsch, Ber. Dtsch. Chem. Ges. 23(1890) 1474-1476.
4. [4]
  L. Knorr, Ber. Dtsch. Chem. Ges. 17(1884) 1635-1642.
5. [5]
  (a) X.Y. Zhang, Z.W. Yang, Z. Chen, et al., J. Org. Chem. 81 (2016) 1778-1785;
  (b) K. Li, J. You, J. Org. Chem. 81 (2016) 2327-2339;
  (c) M. Yousuf, S. Adhikari, Org. Lett. 19 (2017) 2214-2217.
6. [6]
  (a) F. Shi, W. Tan, R.Y. Zhu, G.J. Xing, S.J. Tu, Adv. Synth. Catal. 355 (2013) 1605-1622;
  (b) W. Dai, H. Lu, X. Li, F. Shi, S.J. Tu, Chem. Eur. J. 20 (2014) 11382-11389;
  (c) C.S. Wang, R.Y. Zhu, J. Zheng, F. Shi, S.J. Tu, J. Org. Chem. 80 (2015) 512-520;
  (d) W. Dai, X.L. Jiang, J.Y. Tao, F. Shi, J. Org. Chem. 81 (2016) 185-192;
  (e) Y.M. Wang, H.H. Zhang, C. Li, T. Fan, F. Shi, Chem. Commun. 52 (2016) 1804-1807;
  (f) X.Q. Mou, Z.L. Xu, L. Xu, et al., Org. Lett. 18 (2016) 4032-4035;
  (g) T.Y. Ye, M. Selvaraju, C.M. Sun, Org. Lett. 19 (2017) 3103-3106;
  (h) P. Wu, Ho. Gao, J. Sun, C.G. Yan, Chin. Chem. Lett. 28 (2017) 329-332.
7. [7]
  (a) S.Goyal, J.K.Patel, M.Gangar, K.Kumar, V.A.Nair, RSCAdv.5 (2015)3187-3195;
  (b)N.C.Jadhav, P.B.Jagadhane, H.V.Patile, V.N.Telvekar, Tetrahedron.Lett.54 (2013) 3019-3021;
  (c) C.C. Silveira, S.R. Mendes, G.M. Martins, S.C. Schloesser, T.S. Kaufman, Tetrahedron 69 (2013) 9076-9085;
  (d) S. Sarkar, K. Bera, S. Maiti, S. Biswas, U. Jana, Synth. Commun. 43 (2013) 1563-1570.
8. [8]
  T.V. Kumar, C.R.K. Rao, K. Mukkanti, P.S. Mainkar, Asian J. Chem. 27(2015) 1457-1461. doi: 10.14233/ajchem
9. [9]
  (a) A.S.K. Hashmi, Chem. Rev. 107 (2007) 3180-3211;
  (b) A. Fürstner, P.W. Davies, Angew. Chem. Int. Ed. 46 (2007) 3410-3449;
  (c) E. Jime'nez-Nu'ñez, A.M. Echavarren, Chem. Rev. 108 (2008) 3326-3350;
  (d) G. Dyker, Angew. Chem. Int. Ed. 39 (2000) 4237-4239;
  (e) Angew. Chem. Int. Ed. 49 (2010) 5232-5241;
  (f) L. Zhang, Acc. Chem. Res. 47 (2014) 877-888;
  (g) J. Xie, C. Pan, A. Abdukadera, C. Zhu, Chem. Soc. Rev. 43 (2014) 5245-5256.
10. [10]
  (a) C. Wu, Z.W. Liang, Y.Y. Xu, W.M. He, J.N. Xiang, Chin. Chem. Lett. 24 (2013) 1064-1066;
  (b) H. Yi, A.W. Lei, Chin. Chem. Lett. 26 (226) (2015);
  (c) X.X. Di, J. Zhao, Y. Yu, et al., Chin. Chem. Lett. 27 (2016) 1567-1571;
  (d) F. Zhang, Q. Lai, X. Shi, Z. Song, Chin. Chem. Lett. (2018), doi: http://dx.doi.org/10.1016/j.cclet.2018.05.036.
11. [11]
  (a) D. Wang, R. Cai, S. Sharma, et al., J. Am. Chem. Soc. 134 (2012) 9012-9019;
  (b) D.J. Gorin, B.D. Sherry, F.D. Toste, Chem. Rev. 108 (2008) 3351-3378;
  (c) B. Chandrasekhar, S. Ahn, J.S. Ryu, J. Org. Chem. 81 (2016) 6740-6749.
12. [12]
  (a) D.J. Gorin, F.D. Toste, Nature 446 (2007) 395-403.
13. [13]
  (b) G. Revial, S. Lim, B. Viossat, et al., J. Org. Chem. 65 (2000) 4593-4600;
  (c) A. Palmieri, S. Gabrielli, C. Cimarelli, R. Ballini, Green Chem.13 (2011) 3333-3336;
  (d) A.S.K. Hashmi, Acc. Chem. Res. 47 (2014) 864-876.
14. [14]
  M. Zhang, A. Abdukader, Y. Fu, C. Zhu, Molecules 17(2012) 2812-2822. doi: 10.3390/molecules17032812
15. [15]
  A. Abdukader, Q. Xue, A. Lin, et al., Tetrahedron. Lett. 54(2013) 5898-5900. doi: 10.1016/j.tetlet.2013.08.100
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